Triethylamine → HCID 21770650, compound

HRID 1924068Notes

Reaction equation

HRID 1924068 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[N:18]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].C(OCC)(=O)C.CCN(CC)CC>CO.O.[Fe]>[O:11]1[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21770646HCID 21770646, compound

Product 1

HCID 21770650HCID 21770650, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

2-(4-Nitrophenyl)oxazolo[4,5-c]pyridine (2.261 g, 9.3 mmol), iron powder (2.814 g, 48.0 mmol) and NH4Cl (4.314 g, 80.1 mmol) were refluxed in CH3OH/H2O (4:1, 469 mL) for 6 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel eluted with petroleum ether:ethyl acetate: Et3N=160:40:1 to afford 4-(oxazolo[4,5-c]pyridin-2-yl)benzenamine as a yellow solid (1.215 g, yield: 62%). 1H NMR (400 MHz, DMSO-d6) δ: 6.11 (2H, s), 6.69 (2H, d, J=8.4 Hz), 7.75 (1H, d, J=5.6 Hz), 7.87 (2H, d, J=8.4 Hz), 8.46 (1H, d, J=5.6 Hz), 8.94 (1H, s); MS(ESI) calcd. for C12H9N3O (m/z): 211, found: 212 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by chromatography on silica gel
  4. washeluted with petroleum ether

Sources & evidence

ORD record
ord-a8542a1fca5144dd8e4bfd45af368fe2
Source dataset
uspto-grants-2012_05
Patent number
US08178536B2

Reaction notes

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